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Ashland Vacations

Pack those stellar shades. We have Ashland vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Ashland – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Ashland vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Ashland

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Ashland vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Ashland well.

Ashland Flight + Hotel packages

Top Hotel Deals

See all 693 Properties in Ashland
Warren Conference Center and Inn

Warren Conference Center and Inn

529 Chestnut Street, Ashland
    3.5 out of 5.0
     
     

    Situated on a lake, this hotel is 2 mi (3.2 km) from Ashland State Park and 2.9 mi (4.6 km) from Pinecrest Golf Club. Hopkinton State Park and Framingham State ...

    Warren Conference Center and Inn$102

    Warren Conference Center and Inn$102
    Sheraton Boston Hotel

    Sheraton Boston Hotel

    39 Dalton St, Boston
      4.0 out of 5.0
       
       

      This hotel in Boston's historic Back Bay provides indoor access to the Hynes Convention Center, the Prudential Center, Copley Place malls, numerous shops and ...

      Hampton Inn Boston Waltham

      Hampton Inn Boston Waltham

      135 2nd Ave, Waltham
        2.5 out of 5.0
         
         

        Situated in Waltham, this hotel is within 9 mi (15 km) of Bentley College, Burlington Mall, and Babson College. Harvard Square and Boston College are also within ...

        Hampton Inn Boston Waltham$110

        Hampton Inn Boston Waltham$110
        Copley Square Hotel

        Copley Square Hotel

        47 Huntington Ave, Boston
          4.0 out of 5.0
           
           

          Boston's fashionable and historic Back Bay is the setting for this fully renovated boutique hotel on Copley Square. Newbury Street shops are 2 blocks away, and ...

          Copley Square Hotel$159

          Copley Square Hotel$159
          Boston Marriott Copley Place

          Boston Marriott Copley Place

          110 Huntington Ave, Boston
            4.0 out of 5.0
             
             

            This 38-story Boston hotel is adjacent to 2 malls and a convention center, forming 3 climate-controlled blocks of shops and restaurants; within a half-mile of ...

            Boston Marriott Copley Place$161

            Boston Marriott Copley Place$161
            Copley House

            Copley House

            239 W Newton St, Boston
              3.0 out of 5.0
               
               

              Located in Back Bay, this guesthouse is within a 10-minute walk of Copley Place, Hynes Convention Center, and Boston Symphony Hall. Prudential Tower and Boston ...

              Copley House$165

              Copley House$165
              HYATT house Boston/Waltham

              HYATT house Boston/Waltham

              54 4th Ave, Waltham
                3.0 out of 5.0
                 
                 

                Situated in Waltham, this aparthotel is 3.2 mi (5.1 km) from Bentley College and within 12 mi (20 km) of Burlington Mall and Harvard Square. Boston College and ...

                HYATT house Boston/Waltham$127

                HYATT house Boston/Waltham$127
                Hotel Commonwealth

                Hotel Commonwealth

                500 Commonwealth Ave, Boston
                  4.5 out of 5.0
                   
                   

                  Offering complimentary wireless Internet access throughout, this Boston hotel is located above the Kenmore Square subway station, 2 blocks from Fenway Park, ...

                  Hotel Commonwealth$175

                  Hotel Commonwealth$175
                  The Lenox Hotel Boston

                  The Lenox Hotel Boston

                  61 Exeter Street, Boston
                    4.5 out of 5.0
                     
                     

                    Opened in 1900, this environmentally-friendly Boston hotel is in the historic Back Bay neighborhood, steps from shopping, museums, and Fenway Park. Newbury Street, ...

                    The Lenox Hotel Boston$234

                    The Lenox Hotel Boston$234
                    Best Western Plus Waltham Boston

                    Best Western Plus Waltham Boston

                    380 Winter Street, Waltham
                      3.0 out of 5.0
                       
                       

                      Located in the heart of Technology Square off of route 128, Best Western Plus Waltham Boston is close to Coca-Cola, IBM, Microsoft, and Costco headquarters. ...

                      Best Western Plus Waltham Boston$99

                      Best Western Plus Waltham Boston$99

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.